Sodium hydride → HCID 66850506, compound

Participants

Reaction Steps

A solution of 5.0 g (18.65 mmol) of ethyl 5-bromo-1H-indole-2-carboxylate in 25 ml of dry DMF is added dropwise, at 0° C., to a suspension of 0.96 g (24.24 mmol) of sodium hydride (60%) in 15 ml of dry DMF, maintained under an inert atmosphere. The reaction mixture is stirred at ambient temperature for 1 hour. 4.23 g (2.75 mmol) of 3-fluorobenzyl bromide are subsequently added dropwise, at 0° C. The reaction mixture is then stirred for 18 h at ambient temperature and then diluted with 200 ml of a mixture of water and ethyl acetate (1/1). The resulting mixture is separated by settling out and the aqueous phase is extracted with 2×30 ml of ethyl acetate. The combined organic phases are washed three times with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. The resulting oil is purified by silica gel column chromatography, elution being carried out with a mixture of heptane and ethyl acetate. 5.76 g of the expected product are isolated.

Provenance & Evidence